Synthesis of novel hybrids of pyrazole and coumarin as dual inhibitors of COX-2 and 5-LOX

Shen, Fa-Qian; Wang, Zhongchang; Wu, Song-Yu; Ren, Shen-Zhen; Man, Ruo‐Jun; Wang, Bao‐Zhong; Zhu, Hai‐Liang

doi:10.1016/j.bmcl.2017.07.020

Cited by 54 publications

(21 citation statements)

References 22 publications

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“…Shen, et al [69] reported on synthetic strategies to afford pyrazole moiety containing coumarin sulfonamide structures and evaluated their anti-proliferation activity in vitro. Scaffold (42) was highly biologically active against COX-2 with an IC 50 value of 0.23 ± 0.16 µM when compared to the reference drug celecoxib which had an IC 50 value of 0.41 ± 0.…”

Section: Anti-inflammatory Activities Of Coumarin Sulfonamide Derivatmentioning

confidence: 99%

Coumarin sulfonamide derivatives: An emerging class of therapeutic agents

Irfan

Rubab

Rehman

et al. 2020

Heterocyclic Communications

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Coumarin sulfonamide is a heterocyclic pharmacophore and an important structural motif which is a core and integral part of different therapeutic scaffolds and analogues. Coumarin sulfonamides are privileged and pivotal templates which have a broad spectrum of applications in the fields of medicine, pharmacology and pharmaceutics. Coumarin sulfonamide exhibited versatile and myriad biomedical activities such as anti-bacterial, antiviral, antifungal, anti-inflammatory and anti-cancer. This review article focuses on the structural features of coumarin sulfonamide derivatives in the treatment of different lethal diseases on the basis of structure-activity relationships (SAR). The plethora of research cited in this review article summarizes and discusses the various substitutions around the coumarin sulfonamide nucleus which have provided a wide spectrum of biological activities and therapeutic potential that has proved attractive to many researchers looking to exploit the coumarin sulfonamide skeleton for drug discovery and the development of novel therapeutic agents.

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Section: Anti-inflammatory Activities Of Coumarin Sulfonamide Derivatmentioning

confidence: 99%

Coumarin sulfonamide derivatives: An emerging class of therapeutic agents

Irfan

Rubab

Rehman

et al. 2020

Heterocyclic Communications

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“…However, the inhibition of COX-2/5-LOX has been reported to promote the other pathway of arachidonic acid metabolism as a compensatory mechanism. Considering the similarities of COX-2 and 5-LOX, the dual inhibition thereof to obtain more efficient and safer agents for human cancer treatment is promising, albeit the exact mechanism has not been fully illustrated [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

Antioxidant and Anti-Inflammatory Activities of Hydrolysates and Peptide Fractions Obtained by Enzymatic Hydrolysis of Selected Heat-Treated Edible Insects

2017

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This study investigated the effect of heat treatment of edible insects on antioxidant and anti-inflammatory activities of peptides obtained by in vitro gastrointestinal digestion and absorption process thereof. The antioxidant potential of edible insect hydrolysates was determined as free radical-scavenging activity, ion chelating activity, and reducing power, whereas the anti-inflammatory activity was expressed as lipoxygenase and cyclooxygenase-2 inhibitory activity. The highest antiradical activity against DPPH• (2,2-diphenyl-1-picrylhydrazyl radical) was noted for a peptide fraction from baked cricket Gryllodes sigillatus hydrolysate (IC50 value 10.9 µg/mL) and that against ABTS•+ (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical) was the highest for raw mealworm Tenebrio molitor hydrolysate (inhibitory concentration (IC50 value) 5.3 µg/mL). The peptides obtained from boiled locust Schistocerca gregaria hydrolysate showed the highest Fe2+ chelation ability (IC50 value 2.57 µg/mL); furthermore, the highest reducing power was observed for raw G. sigillatus hydrolysate (0.771). The peptide fraction from a protein preparation from the locust S. gregaria exhibited the most significant lipoxygenase and cyclooxygenase-2 inhibitory activity (IC50 value 3.13 µg/mL and 5.05 µg/mL, respectively).

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“…Coumarins are also used extensively as starting materials in drug discovery, and some coumarin derivatives have potent enzyme inhibition activity [19–21]. For example, the hybrids containing coumarin and other moieties have been used as histone deacetylase weinhibitors [22], cyclo-oxygenase inhibitors [23] and monoamine oxidase inhibitor [24]. Coumarin-chalcone hybrids, are reported as anti-parasitics agents against Plasmodium spp.…”

Section: Introductionmentioning

confidence: 99%

Structure–activity relationship investigation of coumarin–chalcone hybrids with diverse side-chains as acetylcholinesterase and butyrylcholinesterase inhibitors

et al. 2018

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Chalcones containing tertiary amine side-chains have potent activity as acetylcholinesterase (AChE) inhibitors. However, the effects of the location of the tertiary amine groups as well as of other groups on AChE and butyrylcholinesterase (BChE) activity have not been reported. Here, we report the synthesis and testing of 36 new coumarin-chalcone hybrids (5d-7j, 9d-11f, 12k-13m) against AChE and BChE. The nature and position of the chalcone substituents had major effects on inhibitory activity as well as selectivity for AChE over BChE. Compounds with para-substituted chalcone fragments in which the substituents were choline-like had potent activity against AChE and poor activity against BChE, while ortho-substituted analogs exhibited an opposite effect. Replacement of the terminal amine groups by amide, alkyl or alkenyl groups abrogated activity. Compound 5e showed potent inhibitory activity [Formula: see text]) and good selectivity for AChE over BChE (ratio 27.4), and a kinetic study showed that 5e exhibited mixed-type inhibition against AChE. Computational docking results indicate that 5e binds to Trp 279, Tyr334 and Trp 84 in AChE, but only to Trp 82 in BChE. Overall, the results show that coumarin-chalcone hybrids with choline-like side-chains have promising activity and selectivity against AChE and be promising therapeutic leads for Alzheimer's disease.

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Synthesis of novel hybrids of pyrazole and coumarin as dual inhibitors of COX-2 and 5-LOX

Cited by 54 publications

References 22 publications

Coumarin sulfonamide derivatives: An emerging class of therapeutic agents

Coumarin sulfonamide derivatives: An emerging class of therapeutic agents

Antioxidant and Anti-Inflammatory Activities of Hydrolysates and Peptide Fractions Obtained by Enzymatic Hydrolysis of Selected Heat-Treated Edible Insects

Structure–activity relationship investigation of coumarin–chalcone hybrids with diverse side-chains as acetylcholinesterase and butyrylcholinesterase inhibitors

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